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$68+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Apr 24 — May 11
Fri 4/24
Fri 5/1
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.

This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:20 pm
CVG
-
MDW
Nonstop1h 10m
Southwest
Tue 4/2112:50 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Deal found 3/20$174
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
CVG
-
ORD
1 stop17h 50m
Frontier
Wed 4/156:08 pm
ORD
-
CVG
1 stop22h 25m
Frontier
Deal found 3/24$174
This United Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:30 am
CVG
-
ORD
Nonstop1h 34m
United Airlines
Wed 4/296:59 am
ORD
-
CVG
Nonstop1h 24m
United Airlines
Deal found 3/23$175
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:35 pm
CVG
-
MDW
Nonstop1h 15m
Southwest
Wed 6/36:10 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Deal found 3/23$176
This United Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:07 am
SDF
-
ORD
Nonstop1h 40m
United Airlines
Tue 4/286:45 am
ORD
-
SDF
Nonstop1h 25m
United Airlines
Deal found 3/24$177
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:30 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Tue 4/287:40 am
MDW
-
SDF
Nonstop1h 10m
Southwest
Deal found 3/24$177
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
CVG
-
MDW
1 stop9h 00m
Frontier
Sun 4/196:00 am
MDW
-
CVG
1 stop10h 48m
Frontier
Deal found 3/20$180
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:32 pm
CVG
-
ORD
1 stop9h 22m
Frontier
Sun 5/35:50 am
ORD
-
CVG
1 stop11h 26m
Frontier
Deal found 3/23$180
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:19 pm
CVG
-
MDW
1 stop11h 00m
Frontier
Fri 4/179:14 am
MDW
-
CVG
1 stop13h 06m
Frontier
Deal found 3/23$181
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/271:30 pm
CVG
-
ORD
1 stop12h 22m
Frontier
Tue 5/59:42 pm
ORD
-
CVG
1 stop13h 18m
Frontier
Deal found 3/23$181
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:00 am
CVG
-
MDW
1 stop6h 00m
Frontier
Mon 4/206:00 am
MDW
-
CVG
1 stop11h 36m
Frontier
Deal found 3/21$182
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
CVG
-
ORD
1 stop6h 21m
Frontier
Mon 4/205:48 pm
ORD
-
CVG
1 stop14h 34m
Frontier
Deal found 3/20$182

Find flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$174
(Southwest)

One-way from

$68
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$286

Good round-trip deal

$104 or less

Good one-way deal

$175 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Kentucky to Chicago (CHI)
Search Deals
One-way flight from Kentucky to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 25, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 5/9

5:00 pm-5:15 pm

Nonstop1h 15m

Chicago Midway

Mon 5/11

7:00 pm-9:10 pm

Nonstop1h 10m

$191

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 4/18

6:15 pm-6:56 pm

Nonstop1h 41m

Chicago O'Hare Intl

Sat 4/25

6:59 am-9:18 am

Nonstop1h 19m

$191

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 4/22

5:50 pm-10:15 pm

1 stop5h 25m

Chicago Midway

Wed 4/29

8:00 am-12:40 pm

1 stop3h 40m

$195

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 4/14

7:00 am-12:50 pm

1 stop6h 50m

Chicago O'Hare Intl

Wed 4/15

2:40 pm-9:05 pm

1 stop5h 25m

$202

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 5/20

7:15 pm-7:30 pm

Nonstop1h 15m

Chicago Midway

Sat 5/23

7:50 am-10:05 am

Nonstop1h 15m

$211

KnoxvilleChicago

TYS - ORD

TYSORD

Knoxville McGhee Tyson

Sat 4/18

7:50 am-12:49 pm

1 stop5h 59m

Chicago O'Hare Intl

Mon 4/20

1:36 pm-9:20 pm

1 stop6h 44m

$213

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 4/21

11:00 am-12:50 pm

Nonstop1h 50m

Chicago O'Hare Intl

Tue 4/28

2:40 pm-4:20 pm

Nonstop1h 40m

$215

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 4/21

12:40 pm-3:45 pm

1 stop3h 05m

Chicago Midway

Tue 4/28

3:00 pm-4:30 pm

Nonstop1h 30m

$220

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 5/18

3:37 pm-8:26 pm

1 stop5h 49m

Chicago O'Hare Intl

Tue 5/19

9:25 am-1:51 pm

1 stop3h 26m

$230

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 5/1

6:45 pm-11:30 pm

1 stop5h 45m

Chicago Midway

Sat 5/2

2:15 pm-6:30 pm

1 stop3h 15m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, April is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $58). Flying from Kentucky to Chicago in March is currently the most expensive (average of $180). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 25, 2026.

One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 34% on airfare.

What is the cheapest day to fly from Kentucky to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Chicago. Price data was last updated on March 23, 2026.

Travelers seeking maximum savings on their Kentucky to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Kentucky to Chicago

Explore weekly flight availability from Kentucky to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 25, 2026.

The most flights from USKY to CHI are scheduled on a Monday (41 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from Kentucky to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kentucky to Chicago?

    There are many flights that can get you from Kentucky to Chicago in 1h 15m. Fly via Southwest, United Airlines, or Delta to get the fastest option. The distance from Kentucky to Chicago is about 249 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Kentucky to Chicago one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $53. American Airlines flights start at $53 while deals on Contour start at $54 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Knoxville McGhee Tyson - Chicago O'Hare Intl and Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Republic Airways (78%), Copa Airlines (77%), Japan Airlines( 75%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,174 for a flight from Kentucky to Chicago. The cheapest flight overall is $118 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $167.

  • Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

    Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

  • Can I find deals for business class flights from Kentucky to Chicago?

    Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $58). Flying from Kentucky to Chicago in March is currently the most expensive (average of $180). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Chicago

Discover the top 4 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$265FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$247FlexibilityNo cancel feeOn-time63%
ContourCheapest$104Average$170FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$114Average$264FlexibilityNo cancel feeOn-time69%

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